INFLUENCE OF RING SUBSTITUENTS AND MATRIX ON LITHIUM SODIUM SELECTIVITY OF 14-CROWN-4 AND BENZO-13-CROWN-4 COMPOUNDS

被引:20
作者
BARTSCH, RA
GOO, MJ
CHRISTIAN, GD
WEN, XW
CZECH, BP
CHAPOTEAU, E
KUMAR, A
机构
[1] UNIV WASHINGTON,DEPT CHEM,SEATTLE,WA 98195
[2] MILES INC,TARRYTOWN,NY 10591
关键词
FLOW INJECTION; POTENTIOMETRY; CROWN ETHERS; LITHIUM; PICRATE EXTRACTION; POLYMERIC MEMBRANE ELECTRODES; RING SUBSTITUENTS; SODIUM;
D O I
10.1016/0003-2670(93)80581-5
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Binding of Li+ and Na+ by a series of ten benzo-13-crown-4 compounds and a series of fifteen 14-crown-4 derivatives has been assessed by picrate extraction and the response of polymeric membrane electrodes. Variation in cation selectivity was observed when different groups were attached to the central carbon atom of the three-carbon bridges in the ionophores. For the benzo-13-crown-4 series, only weak cation binding and low selectivity was observed in both the picrate extraction and polymeric membrane electrode systems. For the 14-crown-4 series, 6,13-dimethylenyl-14-crown-4 exhibited the highest Li+ selectivity in picrate extraction. In polymeric membrane electrodes, considerably higher Li+ selectivity was observed with 6,6,13-tribenzyl-14-crown-4 and 6,6,13,13-tetraethyl-14-crown-4 than with the commercially available Li+ ionophore, 6,6-dibenzyl-14-crown-4. Lack of correlation for the Li+ selectivities of the 14-crown-4 compounds in the picrate extraction and polymeric membrane electrode systems reveals a profound influence of the matrix on ionophore selectivity.
引用
收藏
页码:285 / 292
页数:8
相关论文
共 13 条
[1]   STEREOCHEMISTRY OF CROWN ETHERS AND THEIR COMPLEXES IN THE SOLID-STATE - C-13 CPMAS NMR AND X-RAY CRYSTALLOGRAPHIC STUDIES OF CONFIGURATIONALLY ISOMERIC DICYCLOHEXANO-14-CROWN-4 ETHERS, DIBENZO-14-CROWN-4 ETHER, AND SOME LITHIUM THIOCYANATE SALTS [J].
BUCHANAN, GW ;
KIRBY, RA ;
CHARLAND, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2477-2483
[2]   FUNCTIONALIZED 13-CROWN-4, 14-CROWN-4, 15-CROWN-4, AND 16-CROWN-4 COMPOUNDS - SYNTHESIS AND LITHIUM ION COMPLEXATION [J].
CZECH, BP ;
BABB, DA ;
SON, B ;
BARTSCH, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :4805-4810
[3]   SYNTHESIS OF BENZO-13-CROWN-4 DERIVATIVES [J].
CZECH, BP ;
ZAZULAK, W ;
KUMAR, A ;
DALLEY, NK ;
JIANG, WM ;
BARTSCH, RA .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (05) :1387-1394
[4]  
CZECH BP, 1992, IN PRESS J HETEROCYC, V29
[5]   COMPARATIVE-STUDY OF MONO-SUBSTITUTED AND DISUBSTITUTED 14-CROWN-4 DERIVATIVES AS LITHIUM IONOPHORES [J].
KATAKY, R ;
NICHOLSON, PE ;
PARKER, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (02) :321-327
[6]   SYNTHESIS AND SELECTIVITY FOR LITHIUM OF LIPOPHILIC 14-CROWN-4 DERIVATIVES BEARING BULKY SUBSTITUENTS OR AN ADDITIONAL BINDING-SITE IN THE SIDE ARM [J].
KIMURA, K ;
YANO, H ;
KITAZAWA, S ;
SHONO, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (12) :1945-1951
[7]   LIPOPHILIC CROWN-4 DERIVATIVES AS LITHIUM IONOPHORES [J].
KITAZAWA, S ;
KIMURA, K ;
YANO, H ;
SHONO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :6978-6983
[8]   DIDECALINO-14-CROWN-4 - HIGHLY LITHIUM ION-SELECTIVE EXTRACTANT [J].
KOBIRO, K ;
MATSUOKA, T ;
TAKADA, S ;
KAKIUCHI, K ;
TOBE, Y ;
ODAIRA, Y .
CHEMISTRY LETTERS, 1986, (05) :713-714
[9]   DECALINO-14-CROWN-4 - NEW TYPE OF LITHIUM ION-SELECTIVE IONOPHORE [J].
KOBIRO, K ;
HIRO, T ;
MATSUOKA, T ;
KAKIUCHI, K ;
TOBE, Y ;
ODAIRA, Y .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (11) :4164-4166
[10]   COMPLEXATION AND SOLVENT-EXTRACTION OF LITHIUM-SALTS WITH 2,3,6,7,9,10-HEXAHYDRO-5H-1,4,8,11-BENZOTETRAOXACYCLOTRIDECIN (BENZO-13-CROWN-4) [J].
OLSHER, U ;
JAGURGRODZINSKI, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1981, (02) :501-505